Ligand-centred Chemistry of Molybdenum Organoimides. Formation of C-C Bonds via Generation of Nitrogen Ylides, Stereospecific Conversion of an Allylimide into Alkylvinylimides, Liberation of Cyanoformate or Amino Acid Esters

DOI: 10.1039/DT9950001973

Source and publish data:

Journal of the Chemical Society, Dalton Transactions p. 1973 - 1984 (1995)

Update date:2022-08-03

Topics:

Authors:

Fairhurst, Shirley A.

Hughes, David L.

Ibrahim, Saad K.

Abasq, Marie-Laurence

Talarmin, Jean

et al. et al.

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/DT9950001973

The range of imides trans-(1+) made from the nitride trans- (dppe = Ph2PCH2CH2PPh2, R1 = H or organic group, R2 = organic group) has been extended; deprotonation of the imide group at the α-carbon gives reactive alkenylamides which have nitrogen ylide character and these are attacked by electrophiles.Stepwise C1 homologation of a methylimide to ethyl- and isopropyl-imides can be achieved by successive deprotonation and methylation steps.The crystal structure of the alkenylamide trans- has been determined, as has that of the imide produced directly from it by C-methylation, trans-2>(1+).Deprotonation at the α-carbon of an allylimide complex gives a species which is regioselectively and stereospecifically attacked by electrophiles at the γ-carbon; when the electrophile is the proton the overall reaction corresponds to a 1,3-prototropic rearrangement of the allylimide to the E-methylvinylimide.Electroreduction of imides in the presence of a source of protons releases the free amine; in this way esters of the amino acids glycine and DL-alanine have been synthesised.Two protons can be removed by base from imides with electron-withdrawing ester substituents and free cyanoformate esters are released from the metal centre by substitution with dinitrogen or CO.

Full text of DOI:10.1039/DT9950001973

View Article Online / Journal Homepage / Table of Contents for this issue

View Article Online

Products guided by the article

Product name:trans-[MoCl(NCHCH₃)(dppe)2]

Cas No:203205-22-5

R&D Labs maybe for 203205-22-5

ShangHai Soyoung Biotechnology Inc

website:http://www.soyoungbio.com

Contact:+86-21-69893009

Address:shanghai
Jintan City Mego Chemical Co., Ltd

Contact:+86-0519-82814387

Address:23# Dengguan Town, Jintan, Jiangsu Province, China
Wuxi Innopal International Trade CO.,LTD

Contact:+86-510-80711901-8003

Address:Room 402,Building 5,Longze Garden,No.17,South huanjiu Road,Yixing City, Jiangsu,China
SAGECHEM LIMITED

website:http://www.sagechem.com

Contact:+86-571-86818502

Address:Room C1301, New Youth Plaza, 8 Jia Shan Road, Hangzhou, China
GenicBio Limited

Contact:+86-(0)21-3770 9035

Address:Room 301, Building 2, Meijiabang Road 1508, Shanghai China

Relevant to this article

New generation dopaminergic agents. 6. Structure-activity relationship studies of a series of 4-(aminoethoxy)indole and 4-(aminoethoxy)indolone derivatives based on the newly discovered 3-hydroxyphenoxyethylamine D₂ template

Doi:10.1021/jm990023s
(1999)
Drug synthesis methods and manufacturing technology: Synthesis of β-phenylhomotaurine

Doi:10.1007/BF02508284
(1999)
Doi:10.1021/ja01013a029
(1968)
Orally active antimalarial 3-substituted trioxanes: New synthetic methodology and biological evaluation

Doi:10.1021/jm970686e
(1998)
Rhodium(III)-catalyzed N-nitroso-directed C-H addition to ethyl 2-oxoacetate for cycloaddition/fragmentation synthesis of indazoles

Doi:10.1002/chem.201404506
(2014)
Stereoselective synthesis of the C-linked analogue of β-D-galactopyranosyl-L-serine

Doi:10.1016/S0040-4020(98)83019-6
(1998)

Article Doi